Every pupil in Oswestry School is assigned to one of four houses. These houses compete in a variety of events for the House Challenge Trophy, which is awarded on Speech Day. As well as competitions in all the main school sports, there is a swimming gala and a sports day. But there are non-sporting events too. For the drama competition each house stages a thirty-minute play and in the music competition there is a song for the whole of each house, as well as solo and small ensemble items.

Once a week each house meets for its own special assembly.

Heads of Houses 2012-13

BURNABY (Mrs Meyer and Mrs Turner) Sam Johnson and Rebecca Adcock

DONNE (Mrs Chidlow) Joe Collinge, Eric Ma and Paige Baker

OSWALD (Miss Ballespi) Robert Clarke and Daisy Tickner

SPOONER (Miss LA Jones) Scott Vallely, Georgina Mercer and Emma Bell

	Burnaby		Donne		Oswald		Spooner
	Pos	Pts	Pos	Pts	Pos	Pts	Pos	Pts
Cross Country - Senior	1	10	4	2	2	6	3	4
Cross Country - Junior
Drama
Football - Junior	4	2	2	6	1	10	3	4
Football - Bellan	=1	8	=1	8	=3	3	=3	3
Football - Senior	3	4	4	2	1	10	2	6
Football - Intermediate	3	4	4	2	1	10	2	6
Sevens Rugby - Intermediate
Rugby - Year 11-13
Rugby - Year 9-10
Music	3	16	1	40	2	24	4	8
Public Speaking	1	10	2	6	4	2	3	4
Quiz - Senior	3	4	1	10	2	6	4	2
Quiz - Junior	4	2	1	10	2	6	3	4
Tennis - Mixed
Tennis - Y7,8 girls
Tennis - Y6,6 girls
Netball - Senior
Sports Day
Swimming - Senior
Total	60		86		77		41

Points System	1st	2nd	3rd	4th
Drama and Music	40	24	16	8
Sports Day	30	18	12	6
Others	10	6	4	2

Colonel Frederick Gustavus Burnaby (1842-1885), was an English soldier, traveller, linguist and adventurer. Burnaby was educated at Harrow, Oswestry School and in Germany. He entered the Royal Horse Guards in 1859 and was made Colonel in 1881.

The Revd. Dr. James Donne (1764-1844) was headmaster of Oswestry School from 1796-1833 and is considered to be one of the school's most distinguished headmasters, who re-established the school's fortunes in the late 18th century and is said by many to be Oswestry School's second founder, after David Holbache.

Oswald (c. 604– 642) was King of Northumbria from 634 until his death, and was subsequently venerated as a Christian saint. Oswald was killed in the battle of Maserfield, said to be on a site near school, fighting Penda of Mercia and his body was dismembered. St Oswald's Well, a holy well of healing was said to have sprung up at the spot where Oswald's arm had landed and is adjacent to the school site, once providing the source of the water for the school's former outdoor swimming pool. The name Oswestry, or "Oswald's Tree", is generally thought to be derived from Oswald's death there and the legends surrounding it.

The Rev Canon William Archibald Spooner DD (1844–1930) was educated at Oswestry School and New College, Oxford, the first non-Wykehamist to be so, and became an Anglican priest and a scholar. During a 60-year association with Oxford University, he became fellow, lecturer, tutor, dean and warden (from 1903) of New College, lecturing ancient history, philosophy (especially Aristotle's ethics) and divinity.